1,1'-Carbonyldiimidazole → HCID 57585130, compound

HRID 2077582Notes

Reaction equation

HRID 2077582 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].C1N=CN([C:26]([N:28]2[CH:32]=[N:31][CH:30]=[CH:29]2)=[O:27])C=1.[O:33]1[CH2:38]CN(CCN)[CH2:35][CH2:34]1>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:26]([NH:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:38][O:33][CH2:34][CH2:35]4)=[O:27])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4082852-MorpholinoethylamineHCID 57584985HCID 57584985, compound

Product 1

HCID 57585130HCID 57585130, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (95 mg, 312 μmol) and CDI (110 mg, 678 μmol) in DMF (1 mL) was heated at 60° C. After sitting overnight, more reagent was added and the mixture was heated for 4 h. 2-morpholinoethanamine (300 μL, 2286 μmol) was added to the mixture, a solution formed. After 3 h, the mixture was cooled to rt and diluted with DCM (15 mL). The solution was washed with H2O (15 mL), dried over Na2SO4 and concentrated. The crude oil was purified by silica gel chromatography with 0-5% (2 N NH3-MeOH) in DCM to give the product as a white powder after hexane washing (45 mg, 31%). MS (ESI, POS. ION) M/Z: calc'd for C21H25ClN6O2S: 460.1. found: 461.1. 1H NMR (400 MHz, chloroform-d) δ ppm 2.49-2.70 (m, 6H) 2.92 (s, 6H) 3.49-3.59 (m, 2H) 3.71-3.83 (m, 4H) 7.49 (s, 1H) 7.56 (d, J=8.03 Hz, 1H) 7.79 (d, J=8.53 Hz, 1H) 7.90 (s, 1H) 8.24 (s, 1H).

Workup

  1. additionmore reagent was added
  2. temperaturethe mixture was heated for 4 h
  3. customa solution formed
  4. waitAfter 3 h
  5. temperaturethe mixture was cooled to rt
  6. washThe solution was washed with H2O (15 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude oil was purified by silica gel chromatography with 0-5% (2 N NH3-MeOH) in DCM

Sources & evidence

ORD record
ord-8dff567eec594612b1f837de12aef850
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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